The invention relates to novel compounds derived from naphth-1-ol which can be represented by formula (I) and comprising at least one cationic group Z of formula (II), their use as coupler for the oxidation dyeing of keratinous fibres, compositions for the oxidation dyeing of keratinous fibres, and in particular human keratinous fibres such as hair, containing them in combination with at least one oxidation base, as well as the oxidation dyeing methods using them.
It is known to dye keratinous fibres and in particular human hair with dyeing compositions containing oxidation dye precursors, in particular para-phenylenediamines, ortho- or para-aminophenols, heterocyclic compounds such as diaminopyrazole derivatives, generally called oxidation bases. Oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, combined with oxidizing products, can give rise, through a process of oxidative condensation, to coloured or colouring compounds.
It is also known that it is possible to vary the shades obtained with these oxidation bases by combining them with couplers or colour modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols, noncationic naphthols or alternatively certain heterocyclic compounds such as for example indolic couplers.
The variety of molecules used in oxidation bases and couplers allows a rich palette of colours to be obtained.
The so-called xe2x80x9cpermanentxe2x80x9d colour obtained using these oxidation dyes must moreover satisfy a number of requirements. Thus, it must be without drawbacks from the toxicological point of view, it must make it possible to obtain shades in the desired intensity and exhibit good resistance towards external agents (light, adverse weather conditions, washing, permanent waving, perspiration, rubbing).
The dyes must also make it possible to cover grey hair and must finally be the least selective possible, that is to say make it possible to obtain the smallest possible differences in colour right along the same keratinous fibre, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
However, the applicant has now just discovered, completely unexpectedly and surprisingly, that the use, as coupler, of novel compounds of the 2-acylaminonaphth-1-ol, 2-amidonaphth-1-ol and 2-sulphonylaminonaphth-1-ol type, comprising at least one cationic group Z of formula (II) as defined below, and which can be represented by formula (I) as defined below, makes it possible to obtain dyeing compositions leading to intense colours, in shades ranging from red to blue and exhibiting, furthermore, remarkable fastness to light, adverse weather conditions, washing, perspiration or permanent waving.
These discoveries form the basis of the present invention.
The first subject of the invention is therefore a compound of the following formula (I), as well as its addition salts with an acid: 
in which:
R1 represents a group chosen from xe2x80x94NR4(Cxe2x95x90O)R5, xe2x80x94NR6SO2R7 and xe2x80x94(Cxe2x95x90O)NR6R8, the radicals R4, R5, R6, R7 and R8 being as defined below;
R2 and R3, which are identical or different, represent a hydrogen atom; a halogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (it being possible for the branch(es) to form one or more carbon-containing rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
it being understood that:
the said radicals R2 and R3 cannot be linked to the benzene ring of formula (I) by an xe2x80x94NHxe2x80x94NHxe2x80x94 bond; and that R2 and R3 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
that R2 and R3 cannot represent a hydroxyl radical or a thio radical;
that R2 and R3 cannot represent, simultaneously, an amino, alkylamino, acylamino or sulphonylamino radical;
Y represents a hydrogen or halogen atom; a group xe2x80x94OR9, xe2x80x94SR9, or xe2x80x94NHxe2x80x94SO2R9 in which R9 represents a C1-C6 alkyl radical, linear or branched (it being possible for the branch(es) to then form one or more rings comprising from 3 to 6 members), unsubstituted or substituted with one or more radicals chosen from the group consisting of a halogen atom, a hydroxyl, C1-C4 alkoxy, amino and amino(C1-C4 alkyl) radical; a phenyl radical, unsubstituted or substituted with one or two radicals chosen from the group consisting of a C1-C4 alkyl, trifluoromethyl, carboxyl, C1-C4 alkoxycarbonyl, halogen, hydroxyl, C1-C4 alkoxy, amino and amino(C1-C4 alkyl) radical; or a benzyl radical;
R4, R6 and R8, which are identical or different, represent a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 15 carbon atoms, linear or branched (it being possible for the branch(es) to form one or more carbon-containing rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
it being understood that the said SO2 group is not directly linked to the nitrogen atom carrying the radical R4 or R6;
it being understood that the group xe2x80x94(Cxe2x95x90O)xe2x80x94 is not directly linked to the nitrogen atom carrying the radical R6;
it being understood that the said radicals R4, R6 and R8 do not contain a peroxide bond or diazo, nitro and nitroso radicals;
it being understood that the radicals R4, R6 and R8 cannot represent a hydroxyl radical, a thio radical, an amino radical, an alkoxy radical, an alkylthio radical;
R5 and R7, which are identical or different, represent a hydrogen atom; a group Z as defined below; a radical comprising from 1 to 20 carbon atoms, linear or branched (it being possible for the branch(es) to form one or more carbon-containing rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms;
it being understood that the said radicals R5 and R7 do not contain peroxide bonds or diazo, nitro and nitroso radicals;
it being understood that R5 cannot represent a hydroxyl radical or a thio radical;
it being understood that R7 cannot represent a thio radical;
it, being understood that the radicals R4 and R5 on the one hand, and the radicals R6 and R8 on the other hand, can, in addition, be linked to form, independently of each other, a saturated or unsaturated ring comprising from 5 to 7 members, consisting of carbon, nitrogen and/or acyl, each member being unsubstituted or substituted with 1 or 2 radicals R, which are identical or different, R being a C1-C8 alkyl radical, linear or branched (it being possible for the branch(es) to then form one or more rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), and in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 group, and in which the carbon atoms may, independently of each other, be substituted with one or more halogen atoms; the said ring containing no peroxide bonds or diazo, nitro and nitroso radicals;
Z is a cationic group represented by the following formula (II): 
xe2x80x83in which:
n can take the value 0 or 1;
B represents an alkyl radical comprising from 1 to 15 carbon atoms, linear or branched (it being possible for the branch(es) to then form one or more rings comprising from 3 to 7 members), which may contain one or more double bonds and/or one or more triple bonds, the said double bonds possibly leading to aromatic groups, and in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom or with an xe2x80x94SO2 radical; and in which one or more carbon atoms may, independently of each other, be substituted with one or more halogen atoms or with one or more groups Z; the said radical B containing no peroxide bond or diazo, nitro or nitroso radicals;
D is chosen from the cationic groups of the following formulae (III) and (IV): 
xe2x80x83in which:
p and q can, independently of each other, take the value 0 or 1;
the radical B is linked to the group D by any one of the atoms of the radical D;
when n=0 and q=0, then the group of formula (IV) can be linked to the compound of formula (I) directly by the nitrogen atom of the quaternary ammonium;
Z1, Z2, Z3 and Z4, independently of each other, represent an oxygen atom; a sulphur atom; a nitrogen atom which is unsubstituted or substituted with a radical R14; a carbon atom which is unsubstituted or substituted with one or two radicals R14, which are identical or different;
Z5 represents a nitrogen atom or a carbon atom which is unsubstituted or substituted with a radical R14;
Z6 can have the same meanings as those indicated below for the radical R14; it being understood that Z6 is different from a hydrogen atom;
the radicals Z1 or Z5 can, in addition, form with Z6 a saturated or unsaturated ring comprising from 5 to 7 members, each member being unsubstituted or substituted with one or two radicals R14 which are identical or different;
R14 represents a hydrogen atom; a group Z; a radical comprising from 1 to 10 carbon atoms, linear or branched, which may contain one or more double bonds and/or one or more triple bonds, it being possible for the said double bonds to then possibly lead to aromatic groups, and in which one or more carbon atoms may be replaced with an oxygen, nitrogen or sulphur atom, or with an SO2 group, and in which one or more carbon atoms may, independently of each other, be substituted with one or more halogen atoms; the said radical containing no peroxide bond or diazo, nitro and nitroso radicals;
it being possible, in addition, for two of the adjacent radicals Z1, Z2, Z3, Z4 and Z5 to form a ring comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different; a nitrogen atom which is unsubstituted or substituted with a radical R14; an oxygen atom; or a sulphur atom;
R10, R11, R12 and R13, which are identical or different, have the same meanings as those indicated above for the radical R14;
it being possible for the radicals R10, R11, R12 and R13 to also form, in pairs with the quaternary nitrogen atom to which they are attached, one or more saturated rings comprising from 5 to 7 members, each member being independently represented by a carbon atom which is unsubstituted or substituted with one or two radicals R14 which are identical or different; a nitrogen atom which is unsubstituted or substituted with a radical R14; an oxygen atom; or a sulphur atom;
Xxe2x88x92 represents an organic or inorganic anion and is preferably chosen from the group consisting of a halide group such as chloride, bromide, fluoride, iodide; a hydroxide; a sulphate; a hydrogen sulphate; a (C1-C6)alkyl sulphate such as for example a methyl sulphate or an ethyl sulphate; an acetate; a tartrate; an oxalate; a (C1-C6)alkyl sulphonate such as for example a methyl sulphonate; an aryl sulphonate which is unsubstituted or substituted with a C1-C4 alkyl radical such as for example a toluoyl sulphonate;
it being understood that at least one of the groups R1 to R3 represents or contains a group Z.
According to the invention, when it is indicated that one or more of the carbon atoms of the radical(s) R1 to R8 can be replaced with an oxygen, nitrogen or sulphur atom or with an SO2 group, and/or that the said radicals R1 to R8 may contain one or more, double bonds and/or one or more triple bonds, that means that it is possible, by way of example, to make the following conversions: 
According to the invention, R2 and R3 preferably represent, independently of each other, a hydrogen or chlorine atom; a group Z; a methyl or methoxy radical; an amino, methylamino, 2-hydroxyethylamino radical; a group xe2x80x94NH(CO)R15 in which R15 represents one of the radicals listed in the group (G1) consisting of a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclopentylmethyl, 3-cyclopentylpropyl, cyclohexyl, 2-cyclohexylethyl, norborn-2-yl, vinyl, 1-methylvinyl, 2-methylvinyl, 2,2-dimethylvinyl, allyl, 3-butenyl, phenyl, methylphenyl, dimethylphenyl, 2,4,6-trimethylphenyl, 4-ethylphenyl, (trifluoromethyl)phenyl, hydroxyphenyl, methoxyphenyl, ethoxyphenyl, acetoxyphenyl, (trifluoromethoxy)phenyl, aminophenyl, 4-dimethylaminophenyl, fluorophenyl, difluorophenyl, fluoro(trifluoromethyl)phenyl, chlorophenyl, dichlorophenyl, bromophenyl, naphth-1-yl, naphth-2-yl, (2-methoxy)naphth-1-yl, benzyl, 4xe2x80x2-methoxybenzyl, 2xe2x80x2,5xe2x80x2-dimethoxybenzyl, 3xe2x80x2,4xe2x80x2-dimethoxybenzyl, 4xe2x80x2-fluorobenzyl, 4xe2x80x2-chlorobenzyl, phenethyl, 2-phenylvinyl, (1-naphthyl)methyl, (2-naphthyl)methyl; tetrahydrofuran-2-yl, furan-2-yl, 5-methyl-2-(trifluoromethyl)furan-3-yl, 2-methyl-5-phenylfuran-3-yl, thiophen-2-yl, (thiophen-2-yl)methyl, 3-chlorothiophen-2-yl, 2,5-dichlorothiophen-3-yl, benzothiophen-2-yl, 3-chlorobenzothiophen-2-yl, isoxazol-5-yl, 5-methylisoxazol-3-yl, 3,5-dimethylisoxazol-4-yl, 1,3-dimethylpyrazol-5-yl, 1-ethyl-3-methylpyrazol-5-yl, 1-tert-butyl-3-methylpyrazol-5-yl, 3-tert-butyl-1-methylpyrazol-5-yl, 4-bromo-1-ethyl-3-methylpyrazol-5-yl, pyridinyl, chloropyridinyl, dichloropyridinyl, 5-(bromo)pyridin-3-yl, piperazin-2-yl, 2-chloro-4-(trifluoromethyl)pyperimidin-5-yl, quinoxal-2-yl, benzofurazan-5-yl; fluoromethyl, difluoromethyl, trifluoromethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, heptafluoropropyl, 1,1,2,2,3,3,4,4-octafluorobutyl, nonafluorobutyl, chloromethyl, chloroethyl, 1,1-dimethyl-2-chloroethyl, 1,2-dichloroethyl, 1-chloropropyl, 3-chloropropyl, 4-chlorobutyl, hydroxymethyl, methoxymethyl, phenoxymethyl, (4-chlorophenoxy)methyl, benzyloxymethyl, acetoxymethyl, 1,2-dihydroxyethyl, 1-phenoxyethyl, 1-acetoxyethyl, 2-(2-carboxyethoxy)ethyl, 1-phenoxyethyl, 1-acetoxyethyl, (methoxycarbonyl)methyl, 2-carboxyethyl, 2-(methoxycarbonyl)ethyl, 2-carboxycyclopropyl, 2-carboxycyclohexane, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, neopentoxy, hexyloxy, cyclopentyloxy, cyclohexyloxy, vinyloxy, allyloxy, propargyloxy, chloromethoxy, 1-chloroethoxy, 2-methoxyethoxy, 4-chlorobutoxy, phenoxy, 4-methylphenoxy, 4-fluorophenoxy, 4-bromophenoxy, 4-chlorophenoxy, 4-methoxyphenoxy, naphth-2-yloxy, benzyloxy; amino, methylamino, ethylamino, propylamino, isopropylamino, butylamino, cyclohexylamino, allylamino, 2-chloroethylamino, 3-chloropropylamino, carboxymethylamino, phenylamino, fluorophenylamino, (trifluoromethyl)phenylamino, chlorophenylamino, bromophenylamino, 4-acetylphenylamino, methoxyphenylamino, (trifluoromethoxy)phenylamino, naphth-1-ylamino, benzylamino, phenethylamino, pyrid-3-ylamino, dimethylamino, 1-pyrrolidinyl and 4-morpholinyl radical; or a group xe2x80x94NHSO2R16 in which R16 represents one of the radicals listed in the group (G2) consisting of the methyl, trifluoromethyl, ethyl, 2-chloroethyl, propyl, 3-chloropropyl, isopropyl, butyl, thiophen-2-yl, hydroxyl, ethoxy, amino and dimethylamino radicals.
Among these radicals, there are more particularly preferred for R2 and R3, independently of each other, a hydrogen atom; a group xe2x80x94Oxe2x80x94Exe2x80x94Dxe2x80x2, xe2x80x94NHxe2x80x94Exe2x80x94Dxe2x80x2, xe2x80x94NH(CO)xe2x80x94Dxe2x80x2, xe2x80x94NH(CO)xe2x80x94Exe2x80x94Dxe2x80x2, xe2x80x94NH(CO)Oxe2x80x94Exe2x80x94Dxe2x80x2, xe2x80x94NH(CO)NHxe2x80x94Exe2x80x94Dxe2x80x2 or xe2x80x94NH(SO2)xe2x80x94Exe2x80x94Dxe2x80x2, in which xe2x80x94Exe2x80x94 represents a xe2x80x94(CH2)qxe2x80x94 arm, q being an integer equal to 1 or 2, and in which Dxe2x80x2 represents the 3-methylimidazolidinium-1-yl, 3-(2-hydroxyethyl)imidazolidinium-1-yl, 1,2,4-triazolinium-1-yl, 1,2,4-triazolinium-4-yl, Nxe2x80x94(C1-C4)alkylpyridinium-2-yl, Nxe2x80x94(C1-C4)alkylpyridinium-3-yl, Nxe2x80x94(C1-C4)alkylpyridinium-4-yl, N-(2-hydroxyethyl)pyridinium-2-yl, N-(2-hydroxyethyl)pyridinium-3-yl, N-(2-hydroxyethyl)pyridinium-4-yl, pyridinium-1-yl, tri(C1-C4 alkyl)ammonium-N-yl, 1-methylpiperidinium-1-yl and 1,4-dimethylpiperazinium-1-yl groups; a methyl, methoxy, amino or methylamino radical; or a group xe2x80x94NH(CO)R17 in which R17 represents one of the radicals listed in the group (G2) as defined above; or a methanesulphonylamino, ethanesulphonylamino or dimethylaminosulphonylamino group.
According to the invention, R4 preferably represents a hydrogen atom or a group A1, A2, A3, A4 or A5, optionally separated from the nitrogen of the group xe2x80x94NR4(Cxe2x95x90O)R5 by a group xe2x80x94(CO)xe2x80x94.
xe2x80x9cGroup A1xe2x80x9d is understood to mean a linear or branched C1-C8 alkyl radical which may carry one or two double bonds or one triple bond, which may be unsubstituted or substituted with a group chosen from a group A2, a group A4, a group A5, which may be unsubstituted or substituted with one or two groups, which are identical or different, chosen from the Nxe2x80x94(C1-C3)alkylamino, Nxe2x80x94(C1-C3)alkyl-Nxe2x80x94(C1-C3)alkylamino, (C1-C6)alkoxy, oxo, alkoxycarbonyl, acyloxy, amide, acylamino, ureyl, sulphoxy, sulphonyl, sulphonamido, sulphonylamino, bromo, cyano and carboxyl groups, and which may be unsubstituted or substituted with one or more hydroxyl, fluoro or chloro groups.
xe2x80x9cGroup A2xe2x80x9d is understood to mean an aromatic group of the phenyl or naphthyl type, which may be unsubstituted or substituted with one to three groups, which are identical or different, chosen from the methyl, trifluoromethyl, ethyl, isopropyl, butyl, pentyl, fluoro, chloro, bromo, methoxy, trifluoromethoxy, ethoxy, propyloxy, acetyloxy, acetyl and cyano groups.
xe2x80x9cGroup A3xe2x80x9d is understood to mean heteroaromatic groups chosen from the furanyl, thiophenyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, isoxazolyl, isothiazolyl, pyrazolyl, pyrazolotriazolyl, pyrazoloimidazolyl, pyrrolotriazolyl, pyrazolopyrimidyl, pyrazolopyridyl, pyridyl, pyrimidyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, indolyl, indolidinyl, isoindolyl, indazolyl, benzotriazolyl, quinolinyl, benzoimidazolyl and benzopyrimidyl groups, the said heteroaromatic groups being unsubstituted or substituted with 1 to 3 radicals chosen from a linear or branched C1-C4 alkyl radical, a C1-C4 monohydroxyalkyl radical, a C2-C4 polyhydroxyalkyl radical, a carboxyl radical, an alkoxycarbonyl radical, a halogen atom, an amido radical, an amino radical and a hydroxyl radical.
xe2x80x9cGroup A4xe2x80x9d is understood to mean a C3-C7 cycloalkyl radical, a norbonyl radical, carrying or otherwise a double bond and unsubstituted or substituted with 1 or 2 radicals chosen from a linear or branched C1-C4 alkyl radical, a C1-C4 monohydroxyalkyl radical, a C2-C4 polyhydroxyalkyl radical, a carboxyl radical, an alkoxycarbonyl radical, a halogen atom, an amido radical, an amino radical and a hydroxyl radical.
xe2x80x9cGroup A5xe2x80x9d is understood to mean a heterocycle chosen from the dihydrofuranyl, tetrahydrofuranyl, butyrolactonyl, dihydrothiophenyl, tetrahydrothiophenyl, tetrahydrothiophenonyl, iminothiolane, dihydropyrrolyl, pyrrolidinyl, pyrrolidinonyl, imidazolidinonyl, imidazolidinethionyl, oxazolidinyl, oxazolidinonyl, oxazolanethione, thiazolidinyl, isothiazolonyl, mercaptothiazolinyl, pyrazolidinonyl, iminothiolane, dioxolanyl, pentalactone, dioxanyl, dihydropyridinyl, piperidinyl, pentalactam, morpholinyl, pyrazoli(di)nyl, pyrimi(di)nyl, pyrazinyl, piperazinyl and azepinyl rings.
Among these radicals, R4 represents more particularly a hydrogen atom; a methyl, ethyl, isopropyl, allyl, phenyl, benzyl, fluorobenzyl, hydroxybenzyl, difluorobenzyl, trifluorobenzyl, chlorobenzyl, bromobenzyl, methoxybenzyl, dimethoxybenzyl, (trifluoromethoxy)benzyl, 3,4-methylenedioxybenzyl, 6-chloropiperonyl, 4-methylthiobenzyl, 4-methylsulphonylbenzyl, 4-acetylaminobenzyl, 4-carboxybenzyl, 1-naphthomethyl or 2-naphthomethyl radical; or a 2-hydroxyethyl, 2-methoxyethyl or 2-ethoxyethyl group.
Still more preferably, R4 represents a hydrogen atom or a methyl radical.
According to the invention, R5 preferably denotes a hydrogen atom, an amino group; a group Z; a group A1, A2, A3, A4 or A5 as defined above, optionally separated from the carbon (at the 2-position) with respect to the amide function of the compound of formula (I) by a group xe2x80x94Oxe2x80x94, xe2x80x94NH, xe2x80x94N(C1-C3)alkyl- or xe2x80x94(CO)xe2x80x94.
Among these radicals, a group Z or a radical chosen from the group (G1) as defined above is more particularly preferred for R5.
Still more preferably, R5 represents a group Z; a radical chosen from the group (G3) consisting of a methyl, ethyl, propyl, allyl, phenyl, tetrahydrofuran-2-yl, furan-2-yl, thiophen-2-yl, pyridinyl, piperazin-2-yl, fluoromethyl, chloromethyl, 2-chloroethyl, methoxymethyl, acetoxymethyl, 1,2-dihydroxyethyl, methoxycarbonyl, 2-carboxyethyl, methoxy, ethoxy, propoxy, allyloxy, 2-chloroethoxy, 2-methoxyethoxy, amino, ethylamino, allylamino, 2-chloroethylamino, pyridylamino, dimethylamino, 1-pyrrolidinyl or 4-morpholinyl radical.
Still more preferably, R5 represents a group xe2x80x94Dxe2x80x2, xe2x80x94Exe2x80x94Dxe2x80x2, xe2x80x94Oxe2x80x94Exe2x80x94Dxe2x80x2 or xe2x80x94NHxe2x80x94Exe2x80x94Dxe2x80x2 in which xe2x80x94Exe2x80x94 represents a xe2x80x94(CH2)qxe2x80x94 arm, q being an integer equal to 1 or 2 and Dxe2x80x2 a group as defined above; or a radical chosen from the group (G4) consisting of a methyl, methoxymethyl, 2-carboxyethyl, methoxy, amino, ethylamino and 1-pyrrolidinyl radical.
When R4 and R5 form a ring, the said ring is preferably chosen from the 2-pyrrolidinon-1-yl, methyl-2-pyrrolidinon-1-yl, 5-carboxy-2-pyrrolidinon-1-yl, 5-methoxycarbonyl-2-pyrrolidinon-1-yl, pyrazolinon-1-yl, succinimid-1-yl, 3,5-diketopyrazolidin-1-yl, oxindolin-1-yl, maleimid-1-yl, isoindole-1,3-dion-2-yl, 2-piperidinon-1-yl and glutarimid-1-yl groups.
According to the invention, R6 preferably represents a hydrogen atom or a group A1, A2, A3, A4 or A5 as defined above.
There is more particularly preferred for R6 a hydrogen atom; a methyl, ethyl, isopropyl, allyl; phenyl, benzyl, fluorobenzyl, hydroxybenzyl, difluorobenzyl, trifluorobenzyl, chlorobenzyl, bromobenzyl, methoxybenzyl, dimethoxybenzyl, (trifluoromethoxy)benzyl, 3,4-methylenedioxybenzyl, 6-chloropiperonyl, 4-methylthiobenzyl, 4-methylsulphonylbenzyl, 4-acetylaminobenzyl, 4-carboxybenzyl, 1-naphthomethyl or 2-naphthomethyl radical; a 2-hydroxyethyl, 2-methoxyethyl or 2-ethoxyethyl group.
Still more particularly, R6 represents a hydrogen atom or a methyl radical.
According to the invention, R8 preferably denotes a group Z; a hydrogen atom or a group A1, A2, A3, A4 or A5 as defined above.
There is more particularly preferred for R8 a group Z; a hydrogen atom; a methyl, ethyl, isopropyl, allyl; phenyl, benzyl, fluorobenzyl, hydroxybenzyl, difluorobenzyl, trifluorobenzyl, chlorobenzyl, bromobenzyl, methoxybenzyl, dimethoxybenzyl, (trifluoromethoxy)benzyl, 3,4-methylenedioxybenzyl, 6-chloropiperonyl, 4-methylthiobenzyl, 4-methylsulphonylbenzyl, 4-acetylaminobenzyl, 4-carboxybenzyl, 1-naphthomethyl or 2-naphthomethyl radical; a 2-hydroxyethyl, 2-methoxyethyl or 2-ethoxyethyl group.
Still more preferably, R8 represents a hydrogen atom or a methyl radical, a group xe2x80x94Dxe2x80x2, xe2x80x94Exe2x80x94Dxe2x80x2, in which xe2x80x94Exe2x80x94 represents a xe2x80x94(CH2)qxe2x80x94 arm, q being an integer equal to 1 or 2, and Dxe2x80x2 a group as defined above.
When R6 and R8 form a ring, the said ring is preferably chosen from the pyrrolidinyl, piperidinyl, morpholinyl, pyrazolyl, isoxazolyl, imidazolyl, thiazolyl, indolyl, indolidinyl, indazolyl, pyrazolotriazolyl, pyrrolotriazolyl, pyrazoloimidazolyl, pyrazolidinyl, thiomorpholinyl, thiazolyl and pyrazinyl groups.
According to the invention, R7 preferably denotes an amino group; a group Z; a group A1, a group A2, a group A3, a group A4 or a group A5 as defined above, optionally separated from the sulphur of the sulphonyl group of the compound of formula (I) by a group xe2x80x94NH or N(C1-C3)alkyl-.
Among these radicals, there are more particularly preferred for R7 a group Z, one of the radicals listed in the group (G4) consisting of methyl, trifluoromethyl, ethyl, 2-chloroethyl, propyl, 3-chloropropyl, isopropyl, butyl, thiophen-2-yl, hydroxyl, ethoxy, amino and dimethylamino radicals.
Still more preferably, R7 represents a group xe2x80x94Dxe2x80x2, xe2x80x94Exe2x80x94Dxe2x80x2 or xe2x80x94NHxe2x80x94Exe2x80x94Dxe2x80x2, in which xe2x80x94Exe2x80x94 represents a xe2x80x94(CH2)qxe2x80x94 arm, q being an integer equal to 1 or 2, and Dxe2x80x2 a group as defined above; a methyl, ethyl or dimethylamino radical.
According to the invention, Y preferably represents a radical chosen from the group comprising: a hydrogen, chlorine, fluorine or bromine atom; the methoxy, ethoxy, propoxy, benzyloxy and phenoxy groups; xe2x80x94OCH2CH2OMe; xe2x80x94OCH2CH2OMe; xe2x80x94OCH2CH2NMe2; xe2x80x94OCH2(CO)OH, xe2x80x94OCH2(CO)OMe, xe2x80x94OCH2(CO)Oet, xe2x80x94SCH2CH2CO2H and NHSO2Me groups.
Among these radicals, there are particularly preferred for Y, the radicals chosen from the group consisting of a hydrogen or chlorine atom or the methoxy, xe2x80x94OCH2(CO)OH or xe2x80x94OCH2(CO)OMe group.
The group D may be chosen in particular from the imidazolinium, thiazolinium, oxazolinium, pyrrolinium, 1,2,3-triazolinium, 1,2,4-triazolinium, isoxazolinium, isothiazolinium, imidazolidinium, thiazolidinium, pyrazolinium, pyrazolidinium, oxazolidinium, pyrazoltriazolinium, pyrazoloimidazolinium, pyrrolotriazolinium, pyrazolopyrimidinium, pyrazolopyridinium, pyridinium, pyrimidinium, pyrazinium, triazinium, benzoimidazolinium, benzoxazolinium, benzothiazolinium, indolinium, indolidinium, isoindolinium, indazolinium, benzotriazolinium, quinolinium, tetrahydroquinolinium, benzoimidazolidinium, benzopyrimidinium, tetra(C1-C4)alkylammonium, dialkylpiperidinium, dialkylpyrrolidinium, dialkylmorpholinium, dialkylthiomorpholinium, dialkylpiperazinium, azepinium and 1,4-diazabicyclo[2.2.2]octanium groups.
Still more preferably, the group D may be chosen from the 3-methylimidazolidinium-1-yl, 3-(2-hydroxyethyl)imidazolidinium-1-yl, 1,2,4-triazolinium-1-yl, 1,2,4-triazolinium-4-yl, Nxe2x80x94(C1-C4)alkylpyridinium-2-yl, Nxe2x80x94(C1-C4)alkylpyridinium-3-yl, Nxe2x80x94(C1-C4)alkylpyridinium-4-yl, N-(2-hydroxyethyl)pyridinium-2-yl, N-(2-hydroxyethyl)pyridinium-3-yl, N-(2-hydroxyethyl)pyridinium-4-yl, pyridinium-1-yl, trialkyl(C1-C4)ammonium-N-yl, 1-methylpiperidinium-1-yl and 1,4-dimethylpiperazinium-1-yl groups.
Among the compounds of formula (I), there are particularly preferred those in which:
i)
the radical R1 represents a radical chosen from the group (G5) consisting of an acetylamino, methanesulphonylamino, amido or methylamido radical, a group xe2x80x94NHxe2x80x94C(O)xe2x80x94CH2xe2x80x94D1, a group xe2x80x94NHxe2x80x94SO2xe2x80x94CH2xe2x80x94CH2xe2x80x94D1, a group xe2x80x94(CO)xe2x80x94NHxe2x80x94CH2xe2x80x94CH2xe2x80x94D1 in which D1 represents a 3-methylimidazolidinium-1-yl, triazolinium-1-yl, pyridinium-1-yl or trimethylammonium-N-yl group;
the radical R2 is at the 5-position and represents a radical chosen from the group (G6) consisting of an amino, methylamino, acetylamino or methanesulphonylamino radical, a group xe2x80x94NHxe2x80x94[C(O)]mxe2x80x94CH2xe2x80x94D1 in which m represents 0 or 1, or a group xe2x80x94NHxe2x80x94SO2xe2x80x94CH2xe2x80x94CH2xe2x80x94D1;
the radical R3 represents a hydrogen atom;
the radical Y represents a radical chosen from the group (G7) consisting of a hydrogen atom, a chlorine radical and a methoxy radical; or
ii)
the radical R1 represents a radical chosen from the group (G5) as defined above;
the radical R2 is situated at the 8-position and represents a radical chosen from the group (G6) as defined above;
the radical R3 represents a hydrogen atom;
the radical Y represents a radical chosen from the group (G7) as defined above; or
iii)
the radical R1 represents a radical chosen from the group (G5) as defined above;
the radicals R2 and R3 represent a hydrogen atom;
the radical Y represents a radical chosen from the group (G7) as defined above.
Among the compounds of formula (I) in accordance with the invention, there may be mentioned most particularly:
3-[(1-Hydroxynaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-5-(2-(3-methyl-1H-imidazol-3-ium-1-yl)acetyl)aminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium dichloride;
3-[(1-Hydroxy-8-(2-(3-methyl-1H-imidazol-3-ium-1-yl)acetyl)aminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium dichloride;
3-[(1-Hydroxy-5-aminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-5-acetylaminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-5-methoxycarbonylaminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-2-acetylaminonaphthalen-5-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-2-methoxycarbonylaminonaphthalen-5-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-5-methanesulphonylaminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-8-aminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-8-acetylaminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-8-methoxycarbonylaminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-2-acetylaminonaphthalen-8-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-2-methoxycarbonylaminonaphthalen-8-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
3-[(1-Hydroxy-8-methanesulphonylaminonaphthalen-2-ylcarbamoyl)methyl]-1-methyl-3H-imidazol-1-ium chloride;
1-[(1-Hydroxynaphthalen-2-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-5-(2-(pyridinium-1-yl)acetyl)aminonaphthalen-2-ylcarbamoyl)methyl]pyridinium dichloride;
1-[(1-Hydroxy-8-(2-(pyridinium-1-yl)acetyl)aminonaphthalen-2-ylcarbamoyl)methyl]pyridinium dichloride;
1-[(1-Hydroxy-5-aminonaphthalen-2-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-5-acetylaminonaphthalen-2-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-5-methoxycarbonylaminonaphthalen-2-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-2-acetylaminonaphthalen-5-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-2-methoxycarbonylaminonaphthalen-5-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-5-methanesulphonylaminonaphthalen-2-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-8-aminonaphthalen-2-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-8-acetylaminonaphthalen-2-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-8-methoxycarbonylaminonaphthalen-2-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-2-acetylaminonaphthalen-8-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-2-methoxycarbonylaminonaphthalen-8-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxy-8-methanesulphonylaminonaphthalen-2-ylcarbamoyl)methyl]pyridinium chloride;
1-[(1-Hydroxynaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-5-(2-(1,4-dimethylpiperazin-1-ium-1-yl)acetyl)aminonaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium dichloride;
1-[(1-Hydroxy-8-(2-(1,4-dimethylpiperazin-1-ium-1-yl)acetyl)aminonaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium dichloride;
1-[(1-Hydroxy-5-aminonaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-5-acetylaminonaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-5-methoxycarbonylaminonaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-2-acetylaminonaphthalen-5-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-2-methoxycarbonylaminonaphthalen-5-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-5-methanesulphonylaminonaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-8-aminonaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-8-acetylaminonaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-8-methoxycarbonylaminonaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-2-acetylaminonaphthalen-8-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-2-methoxycarbonylaminonaphthalen-8-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
1-[(1-Hydroxy-8-methanesulphonylaminonaphthalen-2-ylcarbamoyl)methyl]-1,4-dimethylpiperazin-1-ium chloride;
and their addition salts with an acid.
These novel compounds of formula (I) may be prepared according to methods well known in the state of the art and described for example in Patent Applications or Patents JP95-303798, JP01186859, JP63258843 and DD285095.
The subject of the invention is also the use of the compounds of formula (I) as coupler for the oxidation dyeing of keratinous fibres and in particular human keratinous fibres such as hair.
Another subject of the invention is a composition for the oxidation dyeing of keratinous fibres, and in particular human keratinous fibres such as hair, characterized in that it contains, in a medium appropriate for dyeing:
at least one oxidation base, and
at least one coupler chosen from the compounds of formula (I) as defined above, as well as their addition salts with an acid.
The compound(s) of formula (I) in accordance with the invention and/or the or their addition salt(s) with an acid preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dyeing composition and still more preferably from 0.005 to 6% by weight approximately of this weight.
As indicated above, the oxidation dyeing composition containing the compound(s) of formula (I) in accordance with the invention makes it possible to obtain intense colours in shades ranging from red to blue, and exhibiting, furthermore, remarkable resistance to the various treatments to which the keratinous fibres may be subjected. These properties are particularly remarkable in particular as regards the resistance of the colours obtained to the action of light, adverse weather conditions, washing, permanent waving and perspiration.
The nature of the oxidation base(s) which can be used in the dyeing composition in accordance with the invention is not critical. They are preferably chosen from the oxidation bases conventionally used in oxidation dyeing and among which there may be mentioned in particular para-phenylenediamines, bisphenylalkylenediamines, para-aminophenols, ortho-aminophenols and heterocyclic bases.
Among the para-phenylenediamines, there may be mentioned more particularly by way of example para-phenylenediamine, para-tolylenediamine, 2-chloro-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,5-dimethyl-para-phenylenediamine, N,N-dimethyl-para-phenylenediamine, N,N-diethyl-para-phenylenediamine, N,N-dipropyl-para-phenylenediamine, 4-amino-N,N-diethyl-3-methylaniline, N,N-bis(xcex2-hydroxyethyl)-para-phenylenediamine, 4-N,N-bis(xcex2-hydroxyethyl)amino-2-methylaniline, 4-N,N-bis(xcex2-hydroxyethyl)amino-2-chloroaniline, 2-xcex2-hydroxyethyl-para-phenylenediamine, 2-fluoro-para-phenylenediamine, 2-isopropyl-para-phenylenediamine, N-(xcex2-hydroxypropyl)-para-phenylenediamine, 2-hydroxymethyl-para-phenylenediamine, N,N-dimethyl-3-methyl-para-phenylenediamine, N,N-(ethyl-xcex2-hydroxyethyl)-para-phenylenediamine, N-(xcex2,xcex3-dihydroxypropyl)-para-phenylenediamine, N-(4xe2x80x2-amino-phenyl)-para-phenylenediamine, N-phenyl-para-phenylenediamine, 2-xcex2-hydroxyethyloxy-para-phenylenediamine, 2-xcex2-acetylaminoethyloxy-para-phenylenediamine, N-(xcex2-methoxyethyl)-para-phenylenediamine, and their addition salts with an acid.
Among the para-phenylenediamines mentioned above, there are most particularly preferred para-phenylenediamine, para-tolylenediamine, 2-isopropyl-para-phenylenediamine, 2-xcex2-hydroxyethyl-para-phenylenediamine, 2-xcex2-hydroxyethyloxy-para-phenylenediamine, 2,6-dimethyl-para-phenylenediamine, 2,6-diethyl-para-phenylenediamine, 2,3-dimethyl-para-phenylenediamine, N,N-bis(xcex2-hydroxyethyl)-para-phenylenediamine, 2-chloro-para-phenylenediamine, 2-xcex2-acetylaminoethyloxy-para-phenylenediamine, and their addition salts with an acid.
Among the bisphenylalkylenediamines, there may be mentioned more particularly by way of example N,Nxe2x80x2-bis(xcex2-hydroxyethyl)-N,Nxe2x80x2-bis(4xe2x80x2-aminophenyl)-1,3-diaminopropanol, N,Nxe2x80x2-bis(xcex2-hydroxyethyl)-N,Nxe2x80x2-bis(4xe2x80x2-aminophenyl)ethylenediamine, N,Nxe2x80x2-bis(4-aminophenyl)tetramethylenediamine, N,Nxe2x80x2-bis(xcex2-hydroxyethyl)-N,Nxe2x80x2-bis(4-aminophenyl)tetramethylenediamine, N,Nxe2x80x2-bis(4-methylaminophenyl)tetramethylenediamine, N,Nxe2x80x2-bis(ethyl)-N,Nxe2x80x2-bis(4xe2x80x2-amino-3xe2x80x2-methylphenyl)ethylenediamine, 1,8-bis(2,5-diaminophenoxy)-3,5-dioxaoctane, and their addition salts with an acid.
Among the para-aminophenols, there may be mentioned more particularly by way of example para-aminophenol, 4-amino-3-methylphenol, 4-amino-3-fluorophenol, 4-amino-3-hydroxymethylphenol, 4-amino-2-methylphenol, 4-amino-2-hydroxymethylphenol, 4-amino-2-methoxymethylphenol, 4-amino-2-aminomethylphenol, 4-amino-2-(xcex2-hydroxyethylaminomethyl)phenol, 4-amino-2-fluorophenol, and their addition salts with an acid.
Among the ortho-aminophenols, there may be mentioned more particularly by way of example 2-aminophenol, 2-amino-5-methylphenol, 2-amino-6-methylphenol, 5-acetamido-2-aminophenol, and their addition salts with an acid.
Among the heterocyclic bases, there may be mentioned more particularly by way of example pyridine derivatives, pyrimidine derivatives and pyrazole derivatives.
Among the pyridine derivatives, there may be mentioned more particularly the compounds described for example in Patents GB 1,026,978 and GB 1,153,196, such as 2,5-diaminopyridine, 2-(4-methoxyphenyl)amino-3-aminopyridine, 2,3-diamino-6-methoxypyridine, 2-(xcex2-methoxyethyl)amino-3-amino-6-methoxypyridine, 3,4-diaminopyridine, and their addition salts with an acid.
Among the pyrimidine derivatives, there may be mentioned more particularly the compounds described for example in German Patent DE 2,359,399 or Japanese Patents JP 88-169,571 and JP 91-10659 or Patent Application WO 96/15765, such as 2,4,5,6-tetraaminopyrimidine, 4-hydroxy-2,5,6-triaminopyrimidine, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine, 2,5,6-triaminopyrimidine, and the pyrazolopyrimidine derivatives such as those mentioned in Patent Application FR-A-2,750,048 and among which there may be mentioned pyrazolo[1,5-a]pyrimidine-3,7-diamine; 2,5-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine; pyrazolo[1,5-a]pyrimidine-3,5-diamine; 2,7-dimethylpyrazolo[1,5-a]pyrimidine-3,5-diamine; 3-aminopyrazolo[1,5-a]pyrimidin-7-ol; 3-aminopyrazolo[1,5-a]pyrimidin-5-ol; 2-(3-aminopyrazolo[1,5-a]pyrimidin-7-ylamino)ethanol, 2-(7-aminopyrazolo[1,5-a]pyrimidin-3-ylamino)ethanol, 2-[(3-aminopyrazolo[1,5-a]pyrimidin-7-yl)(2-hydroxyethyl)amino]ethanol, 2-[(7-aminopyrazolo[1,5-a]pyrimidin-3-yl)-(2-hydroxyethyl)amino]ethanol, 5,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,6-dimethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 2,5,N7,N7-tetramethylpyrazolo[1,5-a]pyrimidine-3,7-diamine, 3-amino-5-methyl-7-imidazolylpropylaminopyrazolo[1,5-a]pyrimidine and their addition salts and their tautomeric forms, when a tautomeric equilibrium exists and their addition salts with an acid.
Among the pyrazole derivatives, there may be mentioned more particularly the compounds described in Patents DE 3,843,892, DE 4,133,957 and Patent Applications WO 94/08969, WO 94/08970, FR-A-2,733,749 and DE 195 43 988 such as 4,5-diamino-1-methylpyrazole, 3,4-diaminopyrazole, 4,5-diamino-1-(4xe2x80x2-chlorobenzyl)pyrazole, 4,5-diamino-1,3-dimethylpyrazole, 4,5-diamino-3-methyl-1-phenylpyrazole, 4,5-diamino-1-methyl-3-phenylpyrazole, 4-amino-1,3-dimethyl-5-hydrazinopyrazole, 1-benzyl-4,5-diamino-3-methylpyrazole, 4,5-diamino-3-tert-butyl-1-methylpyrazole, 4,5-diamino-1-tert-butyl-3-methylpyrazole, 4,5-diamino-1-(xcex2-hydroxyethyl)-3-methylpyrazole, 4,5-diamino-1-ethyl-3-methylpyrazole, 4,5-diamino-1-ethyl-3-(4xe2x80x2-methoxyphenyl)pyrazole, 4,5-diamino-1-ethyl-3-hydroxymethylpyrazole, 4,5-diamino-3-hydroxymethyl-1-methylpyrazole, 4,5-diamino-3-hydroxymethyl-1-isopropylpyrazole, 4,5-diamino-3-methyl-1-isopropylpyrazole, 4-amino-5-(2xe2x80x2-aminoethyl)amino-1,3-dimethylpyrazole, 3,4,5-triaminopyrazole, 1-methyl-3,4,5-triaminopyrazole, 3,5-diamino-1-methyl-4-methylaminopyrazole, 3,5-diamino-4-(xcex2-hydroxyethyl)amino-1-methylpyrazole, and their addition salts with an acid.
According to the invention, the dyeing compositions containing one or more para-phenylenediamines and/or one or more heterocyclic oxidation bases are particularly preferred.
The oxidation base(s) preferably represent from 0.0005 to 12% by weight approximately of the total weight of the dyeing composition, and still more preferably from 0.005 to 6% by weight approximately of this weight.
The dyeing composition in accordance with the invention may also contain, in addition to the compound(s) of formula (I) above, one or more additional couplers which may be chosen from the couplers conventionally used in oxidation dyeing and among which there may be mentioned in particular meta-phenylenediamines, meta-aminophenols, meta-diphenols and heterocyclic couplers such as, for example, indole derivatives, indoline derivatives, pyridine derivatives and pyrazolones, and their addition salts with an acid.
These couplers are more particularly chosen from 2-methyl-5-aminophenol, 5-N-(xcex2-hydroxyethyl)amino-2-methylphenol, 3-aminophenol, 1,3-dihydroxybenzene, 1,3-dihydroxy-2-methylbenzene, 4-chloro-1,3-dihydroxybenzene, 2,4-diamino-1-(xcex2-hydroxyethyloxy)benzene, 2-amino-4-(xcex2-hydroxyethylamino)-1-methoxybenzene, 1,3-diaminobenzene, 1,3-bis(2,4-diaminophenoxy)propane, sesamol, xcex1-naphthol, 6-hydroxyindole, 4-hydroxyindole, 4-hydroxy-N-methylindole, 6-hydroxyindoline, 2,6-dihydroxy-4-methylpyridine, 1-H-3-methylpyrazol-5-one, 1-phenyl-3-methylpyrazol-5-one, and their addition salts with an acid.
When they are present, these additional couplers preferably represent from 0.0001 to 10% by weight approximately of the total weight of the dyeing composition and still more preferably from 0.005 to 5% by weight approximately of this weight.
In general, the addition salts with an acid which can be used in the context of the dyeing compositions of the invention (compounds of formula (I), oxidation bases and additional couplers) are chosen in particular from hydrochlorides, hydrobromides, sulphates, citrates, succinates, tartrates, lactates and acetates.
The medium appropriate for dyeing (or carrier) generally consists of water or of a mixture of water and at least one organic solvent for solubilizing the compounds which might not be sufficiently soluble in water. By way of organic solvent, there may be mentioned for example lower C1-C4 alkanols such as ethanol and isopropanol; glycerol; glycols and glycol ethers such as 2-butoxyethanol, propylene glycol, monomethyl ether of propylene glycol, monoethyl ether and monomethyl ether of diethylene glycol, as well as aromatic alcohols such as benzyl alcohol or phenoxyethanol, similar products and mixtures thereof.
The solvents may be present in proportions preferably of between 1 and 40% by weight approximately relative to the total weight of the dyeing composition, and still more preferably between 5 and 30% by weight approximately.
The pH of the dyeing composition in accordance with the invention is generally between 3 and 12 approximately, and preferably between 5 and 11 approximately. It can be adjusted to the desired value by means of acidifying or alkalinizing agents normally used in dyeing keratinous fibres.
Among the acidifying agents, there may be mentioned, by way of example, inorganic or organic acids such as hydrochloric acid, orthophosphoric acid, sulphuric acid, carboxylic acids such as acetic acid, tartaric acid, citric acid, lactic acid and sulphonic acids.
Among the alkalinizing agents, there may be mentioned, by way of example, aqueous ammonia, alkali metal carbonates, alkanolamines such as mono-, di- and triethanolamines as well as their derivatives, sodium or potassium hydroxides and the compounds of the following formula (V): 
in which W is a propylene residue which is unsubstituted or substituted with a hydroxyl group or a C1-C6 alkyl radical; R23, R24, R25 and R26, which are identical or different, represent a hydrogen atom, a C1-C6 alkyl or C1-C6 hydroxyalkyl radical.
The oxidation dyeing compositions in accordance with the invention may also contain at least one direct dye, in particular for modifying the shades or enriching them with glints.
The dyeing composition in accordance with the invention may also contain various adjuvants conventionally used in hair dyeing compositions, such as anionic, cationic, nonionic, amphoteric or zwitterionic surfactants or mixtures thereof, anionic, cationic, nonionic, amphoteric or zwitterionic polymers or mixtures thereof, inorganic or organic thickeners, antioxidants, penetrating agents, sequestering agents, perfumes, buffers, dispersing agents, conditioning agents such as for example modified or unmodified, volatile or nonvolatile silicones, film-forming agents, ceramides, preservatives, opacifying agents.
Of course, persons skilled in the art will be careful to choose this or these possible additional compounds such that the advantageous properties which are intrinsically attached to the oxidation dyeing composition in accordance with the invention are not, or not substantially, impaired by the addition(s) envisaged.
The dyeing composition according to the invention may be provided in various forms, such as in the form of liquids, creams, gels, or in any other form appropriate for dyeing keratinous fibres, and in particular human hair.
The subject of the invention is also a method of oxidation dyeing of keratinous fibres, and in particular human keratinous fibres such as hair, using the dyeing composition as defined above.
According to this method, at least one dyeing composition as defined above is applied to the fibres, the colour being developed at acidic, neutral or alkaline pH with the aid of an oxidizing agent which is added just at the time of use to the dyeing composition or which is present in an oxidizing composition applied simultaneously or sequentially.
According to a preferred embodiment of the dyeing method of the invention, the dyeing composition described above is preferably mixed, at the time of use, with an oxidizing composition containing, in a medium appropriate for dyeing, at least one oxidizing agent present in a sufficient quantity to develop a colour. The mixture obtained is then applied to the keratinous fibres and allowed to act for 3 to 50 minutes approximately, preferably 5 to 30 minutes approximately, after which they are rinsed, washed with shampoo, rinsed again and dried.
The oxidizing agent may be chosen from the oxidizing agents conventionally used for the oxidation dyeing of keratinous fibres, and among which there may be mentioned hydrogen peroxide, urea peroxide, alkali metal bromates, persalts such as perborates and persulphates, and enzymes such as peroxidases, laccases, tyrosinases and oxidoreductases among which there may be mentioned in particular pyranose oxidases, glucose oxidases, glycerol oxidases, lactate oxidases, pyruvate oxidases and uricases.
The pH of the oxidizing composition containing the oxidizing agent as defined above is such that after mixing with the dyeing composition, the pH of the resulting composition applied to the keratinous fibres preferably varies between 3 and 12 approximately, and still more preferably between 5 and 11. It is adjusted to the desired value by means of acidifying or alkalinizing agents normally used for dyeing keratinous fibres and as defined above.
The oxidizing composition as defined above may also contain various adjuvants conventionally used in hair-dyeing compositions and as defined above.
The composition which is finally applied to the keratinous fibres may be provided in various forms, such as in the form of liquids, creams, gels or in any other form appropriate for dyeing keratinous fibres, and in particular human hair.
Another subject of the invention is a multicompartment device or dyeing xe2x80x9ckitxe2x80x9d or any other multicompartment packaging system in which a first compartment contains the dyeing composition as defined above and a second compartment contains the oxidizing composition as defined above. These devices may be equipped with a means which makes it possible to deliver the desired mixture to the hair, such as the devices described in Patent FR-2,586,913 in the name of the applicant.